“It’s really just like he jumped in at the deep end and became this painter,” said Matthew Higgs, the director of White Columns. He was talking about writer Wayne Koestenbaum, who is known for his books on Warhol and Jackie O. On Oct. 27, White Columns will present Mr. Koestenbaum’s first-ever solo show, with about 50 smallish paintings—some brightly colored self-portraits and a smattering of male nudes.

Mr. Higgs first saw Mr. Koestenbaum’s paintings in early 2011 at the Atlanta Contemporary Art Center, where they shared space with works by Leigh Ledare, Tracey Emin and Laurel Nakadate, and immediately had the idea for a show.

Mr. Koestenbaum came to painting by way of writing. “I’ve always looked at painting and written about it and cared about it,” he told Gallerist. “I think when I wrote my biography of Andy Warhol, that was a real chance to apprentice myself to the way a painter proceeded.”

He said that he paints in “the mood of Joe Brainard or John Wesley, but with the procedure and crazy intensity of obsessive repeaters like Yayoi Kusama.”

He doesn’t have any plans to stop writing. He’s actually written two books since he started painting, and one of them, Humiliation—for which he wrote about things like the joys of amputee pornography and masturbating to the image of one of his 20-something students—earned him an art comparison. Literary critic Dwight Garner described the book in The New York Times as “The literary equivalent of Vito Acconci’s Seedbed”(1972), in which Mr. Acconci hid himself under a ramp at the Sonnabend Gallery and masturbated audibly.

“It’s quite risky.” said Mr. Higgs of Mr. Koestenbaum’s decision to show his paintings. “I think most people will come to the work with some pre-existing Wayne Koestenbaum baggage, and then they’ll have to work out what that means in relation to visual art by Wayne.”

“I am nervous about showing the work publicly,” Mr. Koestenbaum admitted. “I’m also entirely ecstatic. It seems like a fantasy of some wild Cinderella kind coming true.”